Skip to Content
Merck
All Photos(1)

Documents

T4080

Sigma-Aldrich

6, 2′, 4′-trimethoxyflavone

≥98% (HPLC)

Synonym(s):

2-(2,4-Dimethoxyphenyl)-2,3-dihydro-6-methoxy-4H-1-benzopyran-4-one, TMF, Trimethoxyflavone

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C18H16O5
CAS Number:
720675-90-1
Molecular Weight:
312.32
MDL number:
MFCD03412381
UNSPSC Code:
12352200
PubChem Substance ID:
329826784
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated
protect from light

color

yellow

solubility

DMSO: >5 mg/mL

storage temp.

room temp

SMILES string

COc1ccc(c(OC)c1)C2=CC(=O)c3cc(OC)ccc3O2

InChI

1S/C18H16O5/c1-20-11-5-7-16-14(8-11)15(19)10-18(23-16)13-6-4-12(21-2)9-17(13)22-3/h4-10H,1-3H3

InChI key

WUWFDVDASNSUKP-UHFFFAOYSA-N

Biochem/physiol Actions

6, 2′, 4′-trimethoxyflavone is a selective aryl hydrocarbon receptor (AHR) antagonist with no partial agonist activity. The role of the transcription factor aryl hydrocarbon receptor (AHR) in biology is still under evaluation and has expanded beyond that of a xenobiotic sensor and regulator of detoxification. Inhibition of AHR activity by antagonists could result in anti-inflammatory actions. 6, 2′, 4′-trimethoxyflavone (TMF) is a pure AHR antagonist. The compound compete with agonists, such as 2, 3, 7, 8-tetrachlorodibenzo-p-dioxin (TCDD) and benzo[a]pyrene (B[a]P), thus effectively inhibiting AHRmediated transactivation of a heterologous reporter and endogenous targets e.g. CYP1A1. TMF also exhibits no species or promoter dependency with regard to AHR antagonism. Thus it represents an improved tool allowing for more precise dissection of AHR function.
The AHR along with immune functions, is also associated with endocrine processes and cancer development.

Preparation Note

6, 2′, 4′-trimethoxyflavone is soluble in DMSO at a concentration that is greater than 5 mg/ml.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Joseph Shailender et al.
Drug development and industrial pharmacy, 44(7), 1109-1119 (2018-02-08)
Design chitosan based nanoparticles for tenofovir disoproxil fumarate (TDF) with the purpose of enhancing its oral absorption. TDF is a prodrug that has limited intestinal absorption because of its susceptibility to gut wall esterases. Hence, design of chitosan based polymeric
Noël J Diepens et al.
Environmental science & technology, 52(15), 8510-8520 (2018-06-22)
We present a generic theoretical model (MICROWEB) that simulates the transfer of microplastics and hydrophobic organic chemicals (HOC) in food webs. We implemented the model for an Arctic case comprised of nine species including Atlantic cod and polar bear as
Antagonism of aryl hydrocarbon receptor signaling by 6, 2?, 4?-trimethoxyflavone
Murray IA, et al.
Journal of Pharmacology and Experimental Therapeutics, 332(1), 135-144 (2010)
Runxia Sun et al.
Environmental pollution (Barking, Essex : 1987), 222, 165-174 (2017-01-04)
Short chain chlorinated paraffins (SCCPs) are under review for inclusion into the Stockholm Convention on Persistent Organic Pollutants. However, limited information is available on their bioaccumulation and biomagnification in ecosystems, which is hindering evaluation of their ecological and health risks.
Isabel Llamas Jansa et al.
Molecules (Basel, Switzerland), 25(4) (2020-02-16)
In order to improve the suitability of NaBH4 as a clean fuel, its decomposition temperature needs to be decreased to below 535 °C, while its hydrogen release must be as high as possible. In this work, the influence of a
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service